GB2546643A - Chromatographic materail and method for preparation thereof - Google Patents

Chromatographic materail and method for preparation thereof

Info

Publication number
GB2546643A
GB2546643A GB1702672.5A GB201702672A GB2546643A GB 2546643 A GB2546643 A GB 2546643A GB 201702672 A GB201702672 A GB 201702672A GB 2546643 A GB2546643 A GB 2546643A
Authority
GB
United Kingdom
Prior art keywords
group
atom
carbon atoms
substrate
ligand
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
GB1702672.5A
Other versions
GB201702672D0 (en
Inventor
Liu Xiaodong
T Williams Richard
Cui Xiao
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Thermo Electron Manufacturing Ltd
Dionex Corp
Original Assignee
Thermo Electron Manufacturing Ltd
Dionex Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Thermo Electron Manufacturing Ltd, Dionex Corp filed Critical Thermo Electron Manufacturing Ltd
Publication of GB201702672D0 publication Critical patent/GB201702672D0/en
Publication of GB2546643A publication Critical patent/GB2546643A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/32—Bonded phase chromatography
    • B01D15/325—Reversed phase
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
    • B01D15/3847—Multimodal interactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
    • B01D15/361—Ion-exchange
    • B01D15/364—Amphoteric or zwitterionic ion-exchanger
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • B01J20/289—Phases chemically bonded to a substrate, e.g. to silica or to polymers bonded via a spacer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3204—Inorganic carriers, supports or substrates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3244—Non-macromolecular compounds
    • B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3244—Non-macromolecular compounds
    • B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
    • B01J20/3257—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such
    • B01J20/3259—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulfur with at least one silicon atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3285—Coating or impregnation layers comprising different type of functional groups or interactions, e.g. different ligands in various parts of the sorbent, mixed mode, dual zone, bimodal, multimodal, ionic or hydrophobic, cationic or anionic, hydrophilic or hydrophobic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C07F7/0872—Preparation and treatment thereof
    • C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/30—Partition chromatography
    • B01D15/305—Hydrophilic interaction chromatography [HILIC]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Silicon Compounds (AREA)

Abstract

A chromatographic materialcomprisinga zwitterionic ligand covalently bound to a substrate, the ligand preferably has a formula II: wherein R1, R2, R3 are independently selected from an oxygen atom that is configured to connect to a substrate atom in the substrate, an oxygen atom that is configured to connect to a silicon atom of an adjacent ligand, a hydroxyl group, a halogen atom, an alkoxy group, a dialkylamino group, an acyl group, an alkyl group, or an aryl group; L1, L2 and L3 are independently hydrophobic moieties; each containing 2 to 30 carbon atoms, wherein there are at least 10 carbon atoms in the combined chain lengths of L1, L2 and L3; X is an O atom, S atom, amide group or sulfonamide group; n is 0 or 1; R4, R5 are independently selected from a hydrogen atom or a hydrocarbon moiety containing 1 to 20 carbon atoms; and Rf is a negatively charged moiety comprising a sulfonic, carboxylic, or phosphonic functional group.
GB1702672.5A 2014-10-29 2015-10-16 Chromatographic materail and method for preparation thereof Withdrawn GB2546643A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14/526,996 US9340562B1 (en) 2014-10-29 2014-10-29 Chromatographic material and method for preparation thereof
PCT/EP2015/073995 WO2016066452A1 (en) 2014-10-29 2015-10-16 Chromatographic material and method for preparation thereof

Publications (2)

Publication Number Publication Date
GB201702672D0 GB201702672D0 (en) 2017-04-05
GB2546643A true GB2546643A (en) 2017-07-26

Family

ID=54364272

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1702672.5A Withdrawn GB2546643A (en) 2014-10-29 2015-10-16 Chromatographic materail and method for preparation thereof

Country Status (6)

Country Link
US (1) US9340562B1 (en)
JP (1) JP6490208B2 (en)
CN (1) CN107106931A (en)
DE (1) DE112015004948T5 (en)
GB (1) GB2546643A (en)
WO (1) WO2016066452A1 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10618920B2 (en) 2016-06-03 2020-04-14 Agilent Technologies, Inc. Functionalized particles having modified phases
JP6531124B2 (en) * 2016-10-07 2019-06-12 株式会社Kri Method for producing sulfobetaine-based silicon compound
CN108114704B (en) * 2016-11-29 2020-01-03 湖南师范大学 Betaine type monolithic column and preparation method thereof
CZ307339B6 (en) * 2017-04-06 2018-06-13 Vysoká škola chemicko-technologická v Praze Multimodal stationary phases for liquid chromatography, a method of their preparation and their use
US20190126167A1 (en) * 2017-11-01 2019-05-02 Dionex Corporation Sulfonamide based anion exchange resins
EP3990141A1 (en) * 2019-06-26 2022-05-04 Waters Technologies Corporation Coatings with immobilized affinity ligands and enzymes and use thereof in liquid chromatography assays
JP7346201B2 (en) * 2019-09-25 2023-09-19 株式会社日立ハイテクサイエンス Amino acid detection method
CN111135808B (en) * 2019-12-30 2023-03-31 纳谱分析技术（苏州）有限公司 Silicon compound, stationary phase and application thereof
CN111250069B (en) * 2020-01-20 2022-03-04 浙江月旭材料科技有限公司 Silica gel chromatographic packing and preparation method and application thereof
JP7435418B2 (en) * 2020-11-20 2024-02-21 信越化学工業株式会社 Organosilicon compounds, their hydrolyzed condensates and coating compositions

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6884345B1 (en) * 1998-11-09 2005-04-26 Knut Irgum Chromatography method and a column material useful in said method
US20060054559A1 (en) * 2004-09-10 2006-03-16 Dionex Corporation Organosilanes and substrate bonded with same
WO2006088760A1 (en) * 2005-02-15 2006-08-24 Dionex Corporation New organosilanes and substrates covalently bonded with same and methods for synthesis and use
US20090202816A1 (en) * 2006-06-06 2009-08-13 Florida State University Research Foundation, Inc. Stabilized silica colloid
EP2210662A2 (en) * 2009-01-23 2010-07-28 AXAGARIUS GmbH & Co. KG Method for producing adsorbent materials for liquid chromatography using zwitterionic silanes

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US4927879A (en) 1988-02-25 1990-05-22 Purdue Research Foundation Method for solid phase membrane mimetics
US5030352A (en) 1990-01-25 1991-07-09 Purdue Research Foundation Coated media for chromatography
JP3351572B2 (en) * 1992-10-05 2002-11-25 井上 聰一 Analyte separation / analysis method by ion chromatography, dual-charged stationary phase for ion chromatography, and analyte separation / analysis method by multifunctional liquid chromatography
US7045059B2 (en) 2003-07-28 2006-05-16 Sielc Technologies Corp Universal bonded phase material for chromatographic separation
JP4086305B2 (en) * 2003-12-02 2008-05-14 株式会社資生堂 Phosphorylcholine group-containing compound and surface modifier comprising the compound
US20060169638A1 (en) 2005-01-31 2006-08-03 Yury Zelechonok Chromatography method for ion detection and analysis
US20100300971A1 (en) * 2005-05-18 2010-12-02 Sequant Ab Zwitterionic stationary phase as well as method for using and producing said phase
US9314712B2 (en) * 2008-05-09 2016-04-19 Dionex Corporation Functionalized substrates with ion-exchange properties
JP5173691B2 (en) * 2008-09-17 2013-04-03 株式会社 資生堂 Hydrophilic interaction chromatography packing
US9169331B2 (en) * 2012-12-21 2015-10-27 Dionex Corporation Separation of glycans by mixed-mode liquid chromatography

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6884345B1 (en) * 1998-11-09 2005-04-26 Knut Irgum Chromatography method and a column material useful in said method
US20060054559A1 (en) * 2004-09-10 2006-03-16 Dionex Corporation Organosilanes and substrate bonded with same
WO2006088760A1 (en) * 2005-02-15 2006-08-24 Dionex Corporation New organosilanes and substrates covalently bonded with same and methods for synthesis and use
US20090202816A1 (en) * 2006-06-06 2009-08-13 Florida State University Research Foundation, Inc. Stabilized silica colloid
EP2210662A2 (en) * 2009-01-23 2010-07-28 AXAGARIUS GmbH & Co. KG Method for producing adsorbent materials for liquid chromatography using zwitterionic silanes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Analytical and Bioanalytical Chemistry, Vol. 402, No. 1, 31 August 2011, Buszewski et al, "Hydrophilic interaction liquid chromatography (HILIC)-a powerful separation technique", pages 231-247 *

Also Published As

Publication number Publication date
JP6490208B2 (en) 2019-03-27
US20160122368A1 (en) 2016-05-05
CN107106931A (en) 2017-08-29
US9340562B1 (en) 2016-05-17
DE112015004948T5 (en) 2017-07-13
JP2018500149A (en) 2018-01-11
GB201702672D0 (en) 2017-04-05
WO2016066452A1 (en) 2016-05-06

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